Shocking Oscar wins: Most unexpected wins in history of Academy Awards

"Moonlight" (2017) - Best Picture

The 89th Academy Awards was marked by one of the most shocking moments in Oscar history. Everything was going smoothly until the announcement of the most anticipated category — Best Picture.

On stage, "La La Land" was declared the winner, and the film’s creators began their acceptance speeches. However, moments later, it was revealed that a mistake had been made — the real winner was "Moonlight".

"Parasite" (2020) - Best Picture

Bong Joon-ho’s "Parasite" made history at the 92nd Academy Awards, becoming the first non-English-language film to win Best Picture.

In addition to the top honor, the film won three more Oscars:

• Best Director,
• Best Original Screenplay,
• Best International Feature Film.

This South Korean thriller, with its sharp social satire, surprised audiences with its masterful storytelling and direction.

Marisa Tomei in "My Cousin Vinny" (1993) - Best Supporting Actress

Marisa Tomei’s victory for her role as Mona Lisa Vito in the comedy "My Cousin Vinny" remains one of the most unexpected wins in Oscar history.

In the film, she plays the witty and charismatic fiancée of Joe Pesci’s character, who helps him defend his cousin in court.

Despite her stellar performance, Tomei competed against Vanessa Redgrave, Joan Plowright, Judy Davis, and Miranda Richardson, all of whom were considered favorites for their dramatic roles.

When Tomei’s name was announced, the audience was stunned, and rumors even spread that presenter Jack Palance had read the wrong name.

"Rocky" (1976) - Best Picture

"Rocky," written by and starring Sylvester Stallone, was another shocking Oscar victory.

The film tells the story of Rocky Balboa, a small-time boxer who gets a once-in-a-lifetime chance to fight the heavyweight champion.

Like its underdog protagonist, the film itself was an underdog in Hollywood—made on a small budget and not considered a serious contender.

However, its raw authenticity and inspiring message captivated audiences, making it one of the most beloved Oscar-winning films of all time.

"Crash" (2006) - Best Picture

The 78th Academy Awards featured one of the most controversial and unexpected wins.

Paul Haggis’s "Crash" won Best Picture, defeating the favorite, "Brokeback Mountain" by Ang Lee.

"Crash" is a multi-layered drama exploring racial tensions, prejudice, and human connections in Los Angeles.

Adrien Brody in "The Pianist" (2003) - Best Actor

At the 75th Academy Awards, 29-year-old Adrien Brody became the youngest actor ever to win Best Actor for his performance in Roman Polanski’s "The Pianist."

Brody played Władysław Szpilman, a Polish Jewish musician struggling to survive during the Holocaust.

His deeply emotional and physically transformative performance shocked audiences, as Brody underwent intense training and extreme weight loss to embody the role.

"Shakespeare in Love" (1999) - Best Picture

The 71st Academy Awards delivered one of the biggest upsets when "Shakespeare in Love" won Best Picture, beating out "Saving Private Ryan" by Steven Spielberg.

The romantic comedy-drama, directed by John Madden, tells a fictional love story about William Shakespeare, which supposedly inspired "Romeo and Juliet."

However, "Saving Private Ryan" was widely considered the frontrunner, with its powerful war drama, intense battle scenes, and deep emotional impact.

Many attribute "Shakespeare in Love’s" victory to the aggressive marketing campaign led by Harvey Weinstein, who was known for influencing Academy votes.

Roberto Benigni in "Life Is Beautiful" (1999) - Best Actor

At the 71st Academy Awards, Italian actor and director Roberto Benigni created one of the most joyous moments in Oscar history.

He won Best Actor for his performance in "Life Is Beautiful," in which he plays Guido Orefice, an Italian Jew who uses humor and imagination to shield his son from the horrors of a Nazi concentration camp.

His win demonstrated that the Academy values performances that transcend cultural boundaries and touch hearts worldwide.

"The Hurt Locker" (2010) - Best Picture

The 82nd Academy Awards was a landmark event as Kathryn Bigelow’s "The Hurt Locker" won Best Picture.

This victory was particularly unexpected, as its main competitor was James Cameron’s "Avatar", which at the time was the highest-grossing film in history.

"The Hurt Locker" is a tense war drama about an elite bomb squad in Iraq, showcasing the psychological and physical toll of combat.

Olivia Colman in "The Favourite" (2019) - Best Actress

At the 91st Academy Awards, audiences were in for a pleasant surprise when Olivia Colman won Best Actress for her role in "The Favourite."

Her portrayal of Queen Anne in this dark historical comedy-drama was both emotional and humorous, capturing the complexities and vulnerabilities of a monarch.

Anna Paquin in "The Piano" (1994) - Best Supporting Actress

The 66th Academy Awards saw one of the biggest surprises when 11-year-old Anna Paquin won Best Supporting Actress for "The Piano."

Directed by Jane Campion, the film follows a mute woman and her daughter who are sent to 19th-century New Zealand for an arranged marriage.

Despite her young age, Paquin delivered a remarkably mature and emotionally profound performance, leaving a lasting impact.

Tilda Swinton in "Michael Clayton" (2008) - Best Supporting Actress

In "Michael Clayton," Tilda Swinton played Karen Crowder, a corporate lawyer involved in covering up unethical practices.

Her performance was chilling yet deeply compelling, capturing the moral dilemmas of corporate corruption.

Her win highlighted the Academy’s appreciation for complex, multi-dimensional characters.

Check out the full list of BAFTA 2025 winners.

Sources: Woke Waves, Wikipedia pages on various Oscar ceremonies, and background information on some of the mentioned actors.